Hydrochloric Acid → 5-Amino-2,1-benzoxaborol-1(3H)-ol

HRID 1425932

反応式

HRID 1425932 の反応式
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[B:8]([OH:11])[O:9][CH2:10][C:6]=2[CH:5]=1)([O-])=O.Cl>CO.[Zn]>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]2[B:8]([OH:11])[O:9][CH2:10][C:6]=2[CH:5]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 68281436HCID 68281436、化合物

生成物 1

HCID 597551995-Amino-2,1-benzoxaborol-1(3H)-ol収率 83%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a solution of 5-nitrobenzo[c][1,2]oxaborol-1(3H)-ol (CII) (360 mg, 2.01 mmol) in MeOH (25 mL) was added Zn dust (1.31 g, 20.11 mmol) and 2 M HCl (30 mL, 60.33 mmol). The reaction mixture was stirred at room temperature for 2.5 h before saturating with 5% aq. NaHCO3 (40 mL). The solids were filtered and filtrate was concentrated under reduce pressure to about 50 mL. The residue was diluted with EtOAc and the phases were separated. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give 5-aminobenzo[c][1,2]oxaborol-1(3H)-ol (CIII) as a brown oil (250 mg, 1.68 mmol, 83% yield, 80% purity). ESIMS found for C7H8BNO2 m/z 149.9 (M+H). The crude product was used without further purification for coupling.

後処理

  1. concentrationbefore saturating with 5% aq. NaHCO3 (40 mL)
  2. filtrationThe solids were filtered
  3. concentrationfiltrate was concentrated
  4. additionThe residue was diluted with EtOAc
  5. customthe phases were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ca8b7b2d4036495fbfda4a54d40dd04a
出典データセット
uspto-grants-2015_01
特許番号
US08933018B2

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